An efficient synthesis of 5-silyl-2,3-dihydrofurans via acid-catalyzed ring-enlargement of cyclopropyl silyl ketones and their functionalization

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• 作者：Mitsunori Honda ; Tomoyuki Naitou ; Hiromitsu Hoshino ; Seiji Takagi ; Masahito Segi and Tadashi Nakajima
• 关键词：Cyclopropyl silyl ketone ; Dihydrofurane ; Ring enlargement ; Heck reaction
• 刊名：Tetrahedron Letters
• 出版年：2005
• 出版时间：2005
• 年：2005
• 卷：46
• 期：43
• 页码：7345-7348
• 全文大小：114 K

文摘

Treatment of cyclopropyl silyl ketones with trimethylsilyl trifluoromethanesulfonate as a strong acid having low nucleophilic counter anion gives the corresponding 5-silyl-2,3-dihydrofuran derivatives, exclusively, regardless of substituents on the cyclopropane ring or silicon atom. The resulting 5-silyl-2,3-dihydrofuran derivatives exhibit both reactivities of the vinylsilane and the cyclic enol ether in the subsequent reaction with electrophilic reagents or Heck type reaction.